


A Skype a Day Keeps the Longing Away

by Coppercurls



Category: Check Please! (Webcomic)
Genre: Established Relationship, M/M, it's another Maine for the summer fic y'all, just wanted to write fluff and family dynamic, the OCs are family members, the rating is only for language, which is pretty mild tbh
Language: English
Status: Completed
Published: 2017-06-24
Updated: 2017-06-30
Packaged: 2018-11-18 06:44:28
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,237
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11285838
Author URL: https://archiveofourown.org/users/Coppercurls/pseuds/Coppercurls
Summary: Will misses Derek a lot during their first summer apart as a couple. So, they Skype. A Lot. Eventually, Will's twin sister decides that it's time to meet this "amazing, beautiful, romantic" boyfriend of his.





	1. Chapter 1

William Poindexter lay on his bed, head hanging off the side, when he realized he was too exhausted from working on his Uncle Elijah’s lobster boat, and then helping out around his Uncle Jay’s mechanic shop to contemplate romance stuff.

“Aoife!” Will yelled out his open door. When he didn’t hear any footsteps, he yelled again. “Aaaooooiiiiffffffffeeeeeeeeeeee!”

A moment later, Will’s twin sister stuck her head into his doorway, her long, wavy red hair swishing back and forth. “’Sup bro?” She said, flinging herself onto his bed, ignoring the fact that he was already there. “And if it’s about your boy again, you owe me a milkshake.”

“Am I being too clingy? I mean, we skyped yesterday, and we’ve been texting most of today, but I want to call him… or skype him. Aoife, stop laughing at me!” Aoife ignored him, choosing instead to poke at his stomach with her toes. “Get off me E!” Will’s attempt to push his sister away turned into a light wrestling match, and Will soon ended up on the floor groaning (Will maintains that he lets Aoife win these tussles).

Aoife looked down at Will as she rearranged herself to sit cross-legged. “My little brother is in love! And you won’t even let me laugh at you for it! And you haven’t even introduced me yet! You know, when I was your age-”

“Yeah, all of five minutes ago.”

“Don’t interrupt. When I was your age, I respected my elders.”

Instead of responding, Will tilted his head toward the door. “Ma!”

“Yeah, Will?” his mom called from somewhere else in their house.

“Has Aoife ever been respectful of her elders?”

The burst of laughter they heard, not just from their mom, but their other siblings, and maybe their dad by the sound of it, seemed to satisfy Will as an answer, and he turned to smirk at Aoife.

“Yeah, yeah, whatever,” she said. “Now get up here and skype your boy so I can see if he’s good enough for you.”

Will snorted, but pulled out his phone to shoot Derek a text. 'Skype?'

He got a reply instantly. 'In a minute, nearly done with dinner'. Will nodded to himself and pulled himself onto his bed next to Aoife, and grabbed his laptop from under the bed in the process. He quickly opened up Skype, then set the computer off to the side.

“So, what should I be expecting? I know his name’s Derek, and that you have got some massive feels for this boy, but other than that, I’ve got nada,” Aoife said, as she pulled her long hair into a quick bun on the top of her head.

“He’s my defense partner.”

“Yes, the one you bitched about for over a year.” She ignored Will’s glare. “You know what, I’ll just ask him!”

“Aoife, if you give him the Spanish inquisition I swear to God…”

The skype alert started ringing out from Will’s laptop, cutting him off. Aoife smiled and bounced quickly in her seat before leaning over her brother to accept the call. After a short buffer, the video connected, showing Will’s beautiful, amazing, and, more importantly, shirtless boyfriend on the screen.

“Willlllllll I’m so happy you-” Derek cut off his enthusiastic greeting as soon as he noticed Aoife, whose eyebrows were raised in amusement. “Um… Hi?”

“Damn, Will, you didn’t say your boy was such a looker,” Aoife said, purposefully not diffusing the situation, enjoying the burning shade of red Will was turning.

“Derek, this is Aoife, my twin. Please put a shirt on,” Will said, trying to school his embarrassment.

“Oh, shit, yeah, one sec,” Derek left the screen as he kept talking. “Didn’t realize you weren’t alone.” He reappeared a moment later, looking bashful, but thankfully, fully clothed.

“And if he was alone?” Aoife said as she waggled her eyebrows suggestively.

Will refused to look at Derek. “E, if you don’t cut this out, you’re never allowed to talk to my boyfriend ever again.”

“But I don’t even know his favorite color and social security number yet!”

Will shoved her off the bed, quickly, before she could retaliate. “I’m so sorry,” he said to Derek.

“Nah, babe, I want to meet your twin,” Derek said, smiling softly at Will. “Could’ve used a warning though.”

“Everyone could use a warning when it comes to Aoife.”

“Stop being rude, I’m right here.” Aoife stood and rejoined Will on the bed. “Hi Derek! I’m Aoife.”

“Nice to meet you Aoife. Now, you’ve gotta tell me, what was this dork like as a kid?”

“Oh my Gooooooood,” Will groaned. Simultaneously, two voices shushed him. “I knew I didn’t want you two to meet. Okay, I’m out, I don’t want to hear you both chirp me.”

“But baaaaaabe,” Derek said, putting on his best puppy dog eyes.

“Dude. Those eyes only work for Chowder. I’ll talk to you later babe, I’m just going to let you two talk for a bit.”

“Don’t worry, bro,” Aoife said, “I’ll give him back to you before I hang up.”

“Please do,” Will said, before turning to Derek. “Miss you.”

“Miss you too, I’ll talk to you soon,” Derek responded.

Will left the room and tried to not be too nervous. As soon as he was out, he sent Derek a quick text, 'Don’t worry, you’ll get on like a house on fire'. After he got the confirmation it had sent, Will made his way downstairs and into the kitchen, where his mom and one of his little sisters were. His mom, Kyra Poindexter, sat at the table, curly blonde hair pulled into a haphazard bun held together with a black pen and a pencil, while she chewed on a red pen, tracing an equation with her free hand. His youngest sister, Saffron, more commonly known as Saffy, stood at the stove, her stick- straight red hair in twin French braids, and she stirred whatever was in the pot in front of her.

“Whatcha making there, Saffy?” Will asked as he slid into the chair across from his mom. 

“Alfredo, without chicken though, Mom didn’t want to go to the store,” Saffy responded, not taking her attention off the sauce she was checking the consistency of before moving it off the burner and turning her attention to the boiling pasta.

“Too bad you don’t have your driving test ‘til Wednesday, huh?” Saffy shot Will a withering glare. She had turned sixteen the week before, but had forgotten to schedule her driving test until too late to get a slot on her birthday itself.

“Where’s Aoife?” Kyra asked, marking a number at the top of the sheet she was grading and circling it before looking up at her son.

“She’s commandeering my boyfriend’s time over skype,” Will grumbled, ignoring Saffy’s laughter.

“That’s your own fault for letting her even know about him,” Kyra smiled, shuffling the next paper to the top for her to grade.

“I want to meet your boyfriend too!” Saffy said. “I have to figure out who would date you.”

“Aoife beat you to it Safs, better luck next time,” Will said absently, ignoring his sister’s taunts. He grabbed half of his mother’s ‘to grade’ stack and an extra pen lying nearby, before marking at it. The school had switched to a schedule that had a shorter summer break, with more breaks in between, just a year ago, and Will did not understand it. All he knew is that he’d been out of school two weeks already, and his mom’s school didn’t even have finals until the next Wednesday.

Because of his distraction with grading high school algebra, Will didn’t notice Saffy pinch neatly through a piece of pasta, and rush to get it into the strainer. He did notice, however, when Saffy bolted out of the kitchen and up the stairs.

“Saf…?” Will started, but Kyra cut him off.

“Bring his computer down! I want to meet Derek too,” she shouted after her youngest daughter.

Will buried his face in his arms with a groan. Needless to say, this was not how he’d pictured Derek meeting his family.

“Maaaaaaaa,” he groaned. “You betrayed me! See if I ever help you with grading again.”

Her laughter joined in chorus with two pairs of feet thumping down the stairs and another person’s laughter, laughter that sounded tinny through laptop speakers but still managed to make Will’s heart beat a little faster.

In no time, Will’s laptop (and Derek’s face) was situated on a counter, and the four Poindexters in the room had crowded in front of it to fit in the frame.

“Hey, Derek,” Will said, smiling subconsciously at his boyfriend.

“Hey, Will,” Derek responded softly, and for a moment, Will just stared at him smiling, until Saffy’s elbow dug into his side.

“Introduce us!” She said.

Will had barely started when more people entered his kitchen. His father, Ronan, and his seventeen (nearly eighteen) year old sister, Emma, came into the kitchen and found space in the skype call as well.

“Sorry we’re late,” Ronan said, mirth filling his voice, “I was working with Em’s strumming technique.”

Will sighed. “No problem, Dad, we haven’t even started introductions.” He looked back at Derek, who smiled encouragingly. “Okay, family, this is Derek, my boyfriend. Babe, the runt is Saffy, the dark haired one is Emma, you’ve met Aoife, and this is my mom, Kyra, and my dad, Ronan.”

“Looks like the whole gang is there,” Derek commented, his heartfelt smile from earlier settling back into his normal ‘chill’ one.

“Not quite,” Will laughed, “Keagan won’t be in town until July, and I think he’s bringing his girlfriend and their son along.”

“We don’t use the term ‘full house’ around here lightly,” Kyra said.

“I can see that,” Derek said, and Will saw something pass over his face for a moment, something like wistfulness.

“Do you have a lot of family?” Ronan asked.

“Not much, just my moms and my sister Penelope, and they’re all out of town, or I’m sure they’d want to join in here,” Derek said, and his charm felt a bit off, but only Will seemed to notice.

“You’re all alone? In New York City?” Kyra asked.

“Yep, but don’t worry about me, my moms have always travelled a lot. I know the City really well, and there’s plenty of museums and bookstores to keep me busy.”

“Cool,” Emma said.

“Yeah, how’d someone so cool end up with Billy here?” Saffy asked.

“Saffron!” Kyra exclaimed, and Will just shoved her head aside, feeling the part of him that asked that question frequently spike with curiosity.

“If I knew he had such amazing sisters, I may have dated him sooner,” Derek said, causing Saffy to blush and Aoife to roll her eyes. “But he’s really too good for me.” 

Will felt his face go red-hot, and heard the snickers from all three of his sisters, but he just looked at Derek, who was suspiciously looking away from the camera.

The conversation continued for a few minutes before Ronan said, “Alright, everyone, Saffy made dinner, and it’s getting cold. It was a pleasure to talk to you, Derek, I hope we meet officially soon, Will, we’ll get your plate out as you say goodbye.”

Will flushed again slightly, and waited until everyone had the chance to say farewell. Once that was finished, he picked up his laptop and made his way quickly to his room, shutting his door behind him and flopping onto his bed, laptop still held in front of him, emitting Derek’s laughter over Will’s long groan.

“Will. Dude. Bro. Babe,” Derek said. “Your family is the best.”

Will glares up at him. “That may have been the most embarrassing time of my life.”

“You’ve totally done more embarrassing stuff to try and impress me. You can’t even lie about it, Chowder was present most of the time.”

“Ughhhh shut up.” Will looked at Derek and started to smile.

“Chill.” Will stopped smiling quickly, though it was a bit forced.

They sat in silence for a moment before Will remembered why he wanted to skype in the first place. So he could talk to his boyfriend.

“How was your day?” Will asked, watching Derek flop back onto his bed.

“Same old, same old. I went back to the MOMA and looked at that exhibit I was telling you about. What about you?”

“Just work. We got a good haul today, and Uncle Jay was out today, so the shop was pretty much peaceful, except…” and Will began to regale Derek with tales of customers, and Derek laughed, and chimed in with weird things he saw while in the city, and about the most ‘transcendental street performer’.

Will was in the middle of talking about some kids rant on his math homework his mom had graded, when Derek’s phone pinged.

“Huh,” he frowned, “I’m getting a message.”

“Chowder?” Will asked, with a smirk.

“Um, no. Aoife, actually. She tells me to tell you to get your butt down to dinner.”

Will’s eyebrows raised. “You gave Aoife your number?”

“Yeah. She’s chill, and she’s giving me chirping material,” Derek smiled at Will, and ran his fingers through his hair. “Sounds like you should go, though.”

“Yeah, probably, I’m going to have to face their chirps eventually.”

“Bye, babe, I’ll text you later.”

“Bye.” 

And Will leaned forward and ended the call, only taking a moment to imagine kissing Derek goodbye before he got up and went to join his family for dinner.


	2. Chapter 2

The chirps Will got for the first few days after his family met Derek were constant, to the point where Keagan called him up and asked when his son would meet his new uncle. Needless to say, Derek found it all hilarious.

“Babe, your family’s so great,” Derek said during their (now daily) Skype call. “Did I tell you about the snap Aoife sent me?”

“I think you like my family more than you like me,” Will complained. “You’ve definitely talked to Aoife more today.” Will fake pouted, fighting laughter at the look of outrage on Derek’s face.

“It’s just because Aoife was waitressing today! You don’t text me when you’re out wrangling lobsters.”

Will laughed at that, the kind of laugh where his face was all scrunched up but no sound escaped. “You make it sound like some Steve Irwin shit.”

“Is it not?” Derek asked, his own laughter loud and barking. After far too long (it really wasn’t that funny), silence settled, wherein Will just looked at Derek, and soon noticed that Derek was notably not looking at him.

“What’s wrong?” Will asked, his teeth chewing lightly at the inside of his lower lip. Derek always said he liked to look at Will, and him avoiding it was a cause for concern.

“Well… I’m probably not going to be able to text you at all tomorrow. Or, at least, a lot less than usual.”

“Why’s that? I didn’t think you had any plans until August?”

“I didn’t, but, you know Penny-”

“Your sister.”

“Yeah, she’s getting a few days off unexpectedly, so I’m going to drive down to DC to visit.” There was a hesitant smile on Derek’s face. 

“That’s great, dude! You don’t need to feel bad about that at all! I know how put out you were when you didn’t think you’d be able to see her this summer.”

“Yeah,” Derek’s smile didn’t grow though, it stayed the same, just as uncertain as before. 

“Are your moms still down there?”

“Nah, they left yesterday, off to Morocco. Since Momma was born there, her company thought she’d be more persuasive in some deal. And Mami has time off stored up, and it wasn’t a bad time to cash it in.”

“Don’t worry, Der, you’ll see them before we’re back at Samwell.”

“Hopefully.” Then Derek changed the topic. “How’ve you been? What’s been new in Poindexterville?”

Will narrowed his eyes slightly. “You do know it’s not actually called that, right?”

“Psh, nahhh,” Derek said, repositioning his laptop so that it still showed his face while he lay on his stomach.

“You think you’re so cute,” Will said with a light eye roll and a smile.

“You think so too,” Derek said. The two shared a moment, soft smiles and softer eyes, before Will finally began to talk about his day.

“Well, Mom’s been after us all to clean the house, which is weird cause no one is visiting until Keagan comes up next week, but what’s weirder is that my sisters don’t seem to be fighting her on it…”

~~~

It was a little while after Will hung up with Derek that Aoife came into his room, grabbing his desk chair and sitting on it, backwards, right next to his bed.

“Bro, when do you get off tomorrow?” She said, her face resting on her crossed arms on top of the chair back.

“Probably around 3, and Jay said he’d be good with just Saffy in the store tomorrow, so I was going to have some down time, for once.” Will raised his eyebrows at her warily. “Why?”

“You know that guy at the diner that I told you about? The one who’s really bad at flirting?” Will nodded. “He asked me out today, at the end of my shift, and I turned him down, but I work noon ‘til seven tomorrow, and he works four ‘til close, and I don’t think he’ll try anything, but it’s the crap manager tomorrow, and I know he won’t stop anything, and-”

Will cut her off. “I can come in as soon as I shower tomorrow. There’s a book that Nursey recommended that I’ve been meaning to read. Might as well read it at the diner.” Aoife started to thank him, but Will spoke again before she could. “I expect free French fries though. And a milkshake.”

Aoife made a face, but nodded. “Deal. Thanks, Billy, knew I could count on you.”

She shoved his chair back under his desk and was out of his room before he could say anything. As his door was closing, he glimpsed Emma and Saffy crouched in the hallway next to his room, and once his door was closed, he heard giggle. He sighed, resigned. His sisters were up to something.

~~~

Will munched on a French fry, idly watching Aoife balance empty dishes on her way back to the kitchen. He had tried reading the book Derek told him to read, but it was hard to follow, and the main character was a bit of a dick, so it was taking him some time to get into. Aoife seemed to be having a calm shift, and she wasn’t getting bothered by that prep line boy, so Will was starting to wish he was home with some shitty drama on TV, one he’d deny watching if he was ever asked.

He glanced back at the book in front of him, rereading a sentence about a “chrono-synclastic infundibulum” before he glanced down at his phone, to check the time, and hope Derek might’ve texted him. It was only 6:04, and he hadn’t gotten a text from Derek, but he decided to send him one anyways.

‘Does this book ever make sense?’

Surprisingly, he got a response only a few minutes later. ‘You’re reading it?!?’

Will laughed softly. ‘That doesn’t answer my question, pearl of my heart.’

‘It isn’t supposed to make sense, the story’s still really riveting. Suspension of disbelief, babe.’ A moment later, another text came in, ‘Have I ever told you how happy I am you stopped calling me a ‘mother fucking hipster shit’ when you thought I was being pretentious? Mushy pet names are much better.’

Will snorted, sending a little bit of milkshake into his nose. After coughing for a moment, he responded. ‘Aren’t you supposed to be with your sister? What’re you chirping me for?’

‘Yeah, I’ll stop being a rude guest now :P Talk to you later.’

Setting aside his phone, Will turned his attention to his book, and managed to read about five or so more pages (it didn’t make much sense, but he liked the flow) before he noticed someone slide into the booth across from him and steal one of his fries. He looked at Aoife and raised his eyebrows at her silently.

She shrugged. “Got off early, the last occupied table in my zone cleared out. But I wanna eat some fries, so we’re going to chill for a minute.”

“You’ve been talking to Derek too much,” Will said, digging the cherry out of the bottom of his milkshake glass with his straw.

“And you haven’t?” Aoife laughed, mouth partially full of half chewed potato. 

Will’s face scrunched in disgust. “This is why we can’t have nice things.”

“Oh, hush, I was just the paragon of social grace for, like, seven hours, I deserve a break.”

Will chuckled, but let the topic slide. “Sure, E. Things with that guy weren’t awkward?”

“Ugh, don’t remind me, he absolutely refused to interact with me! Like, when he had to give me my orders, he just shoved them in my general direction! Why are boys so sensitive? You would think I cursed him with erectile dysfunction or something with the way he was acting,” Aoife grumbled, and Will rolled his eyes, thinking about how much he’s missed his sister while he’s been away for college.

Abruptly, Aoife pulled her phone out of her bra, reading something and smiling. “Come on, time to go.”

Will’s eyes narrowed. “What? Don’t you have your own car to drive? What are you planning?”

“Dad dropped me off today, give me your keys, I’m driving.”

She grabbed the keys out of Will’s hands and jumped into the car, haphazardly pulling out of the parking spot as soon as Will closed his door. She then refused to talk for the rest of the drive, just smiling a smile that scared Will more than it should have.

The drive passed in that strange, one sided silence, and by the time they pulled into their driveway, Will was nervous to get out of the car. 

“This isn’t going to be like the time you guys got Saffy to hide under my bed and grab my ankles once it was dark, is it?”

“Will. Bro. Twinniest of twins. Get out of the car.”

Will cocked one eyebrow, but slowly unbuckled his seatbelt. Aoife hopped out of the car and ran around it to yank Will’s door open and gestured at him to get out. He did, trying to convey his incredible mistrust to her through his face.

She looked him up and down once, before straightening the collar of the flannel he had on. His face contorted more. “Dude. Stop making that face, you look constipated.” She ran her fingers through his hair quickly, then licked her fingers and attempted to style it, tch-ing at his noises of protest. 

Once his appearance was up to par with whatever criteria she was judging him on, she nodded, hands on her hips, and shoved him towards the door.

“Go inside,” she said when they had reached the porch, “and have fun!” She then turned around, got into his car, and drove away.

After shooting off a quick text to Derek, ‘My family is fucking ridiculous’, Will sighed and decided to do what Aoife had told him to, and he braced himself for whatever was about to happen.

His house was calm when he walked in, cleaner than normal, and a smell drifted amicably out of his kitchen. Frowning, he realized that it didn’t smell like anything his Ma normally cooked, but it still smelled familiar, somehow, and it smelled a little bit like home. He followed his nose to the kitchen, and things began to make sense when he saw a platter of Derek’s momma’s couscous.

More importantly, he saw Derek standing there, fussing over plating.

Will stood there a moment, smile growing as bright as the sun on his face. It’d only been a few weeks since he last saw his boyfriend, but even that was too long. Derek turned, and saw Will standing, barely through the doorway, and a nervous smile bloomed on his face.

“Will,” he said like a breath, but he started rambling just a moment later. “I’m sorry for not telling you, but I missed you, and I thought it’d be a nice surprise, and your family said you seemed to be missing me too and they helped me plan it, and they said you’d like me here but if you don’t, I can leave, and I’m really sorry, but we were apart, and I started to think that I might love you and I needed to tell you in person, and I didn’t know when I’d see you again, but I knew you needed to know-”

“Nurse,” Will said, the smile on his face aching. “I love you too.”

With that, he stepped into Derek’s space and cupped his face in his hands. For a moment, one moment that clung to reality stronger than all other moments, they stared into each other’s eyes. 

Then they kissed. 

 

Outside the kitchen window, a group of five people cheered silently and made disgusted faces (in Saffy’s case), and quietly crept away from their house. They liked their Will happy, and Derek seemed to do that better than anyone else.

**Notes for the Chapter:**

> I never said this wasn't going to be sickly sweet fluff  
> If I did, I lied.  
> (The book Will is reading on Derek's recommendation is "The Sirens of Titan" by Kurt Vonnegut)
> 
> And that's it!  
> I kind of like these family head canons, so I might write more with them, but who knows tbh
> 
> I hope you liked it, and kudos and comments are always appreciated!  
> Hit me up at the tumblr brain-patterns if you wanna talk!

**Author's Note:**

> Thanks for reading, everyone! There should be at least one more chapter of this, but there might be more based on inspiration and interest.  
> Please let me know of any issues you see, and let me know what you thought!
> 
> Here's a quick family breakdown:  
> Poindexters:  
> Ronan- Will's dad, carpenter, likes to play guitar, has dark hair and dark eyes  
> Kyra- Will's mom, high school math teacher, likes to paint, curly blonde hair and grey eyes  
> Keagan- Will's only brother, oldest child, has a kid (Daniel) with his long-term girlfriend (May), is a nurse, 24yo, looks like his mom  
> Aoife (pronounced Efa)- Will's twin, looks like him (but her eyes are dark), is taking community college classes while she works as a welder and a waitress (she wants to open a bookstore one day, or become a librarian, but she didn't get any scholarships so she's saving first), named after her mom's grandma, 21yo  
> Will- this fic takes place after his junior year, 21yo  
> Emma- Just finished high school, got a piano scholarship to Carnegie Conservatory, looks like her dad (even his bushy eyebrows, which she is growing to love), 17 (nearly 18) yo  
> Saffron (aka Saffy)- Will's youngest sister Doesn't really know what she wants to do in life, but she helps her dad with carpentry a lot, as well as being a permanent employee of her Uncle Jay's mechanic shop, has red hair lighter than Will's and her mom's eyes  
> Nurses:  
> Tatiana- Derek's momma, began her transition when Derek was five, is second in command in some fancy ass company, loves to cook (her couscous is to DIE for)  
> Dora- Derek's mami, worked in federal government for a long time but has downsized to local so she doesn't spend as much time away from home, goes dancing often (all styles, but her favorite is the salsa)  
> Penelope- Derek's sister, is a translator for the federal government, hopes to become an ambassador, has weekly calls with her brother, 23yo  
> Derek- this takes place after his junior year,21yo
> 
> Yes, I am aware this is too much headcanon for such a short fic, but I love them all?
> 
> Feel free to hit me up for anything, either here, or at my tumblr, brain-patterns


End file.
